EA027231B1 - Способ получения бисфосфоновых кислот - Google Patents
Способ получения бисфосфоновых кислот Download PDFInfo
- Publication number
- EA027231B1 EA027231B1 EA201300893A EA201300893A EA027231B1 EA 027231 B1 EA027231 B1 EA 027231B1 EA 201300893 A EA201300893 A EA 201300893A EA 201300893 A EA201300893 A EA 201300893A EA 027231 B1 EA027231 B1 EA 027231B1
- Authority
- EA
- Eurasian Patent Office
- Prior art keywords
- acid
- phosphorylation
- mixture
- phosphorus trichloride
- unsaturated
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 28
- 239000002253 acid Substances 0.000 title claims abstract description 24
- 150000007513 acids Chemical class 0.000 title abstract description 9
- 238000002360 preparation method Methods 0.000 title abstract description 6
- 230000026731 phosphorylation Effects 0.000 claims abstract description 13
- 238000006366 phosphorylation reaction Methods 0.000 claims abstract description 13
- 239000003153 chemical reaction reagent Substances 0.000 claims abstract description 7
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 16
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 13
- 125000005842 heteroatom Chemical group 0.000 claims description 12
- 239000011541 reaction mixture Substances 0.000 claims description 10
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 claims description 10
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 8
- 229920006395 saturated elastomer Polymers 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- -1 bromine anhydride Chemical class 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- 239000012359 Methanesulfonyl chloride Substances 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 claims description 3
- 239000007858 starting material Substances 0.000 claims description 3
- UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 claims description 3
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- HCUYBXPSSCRKRF-UHFFFAOYSA-N diphosgene Chemical compound ClC(=O)OC(Cl)(Cl)Cl HCUYBXPSSCRKRF-UHFFFAOYSA-N 0.000 claims description 2
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 abstract description 8
- 150000004820 halides Chemical class 0.000 abstract description 6
- 239000000047 product Substances 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 229940122361 Bisphosphonate Drugs 0.000 description 3
- 150000004663 bisphosphonates Chemical class 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- QAFBDRSXXHEXGB-UHFFFAOYSA-N imidazol-1-ylacetic acid Chemical compound OC(=O)CN1C=CN=C1 QAFBDRSXXHEXGB-UHFFFAOYSA-N 0.000 description 3
- 239000008194 pharmaceutical composition Substances 0.000 description 3
- XRASPMIURGNCCH-UHFFFAOYSA-N zoledronic acid Chemical compound OP(=O)(O)C(P(O)(O)=O)(O)CN1C=CN=C1 XRASPMIURGNCCH-UHFFFAOYSA-N 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- WGNUNYPERJMVRM-UHFFFAOYSA-N 3-pyridylacetic acid Chemical compound OC(=O)CC1=CC=CN=C1 WGNUNYPERJMVRM-UHFFFAOYSA-N 0.000 description 1
- 206010006187 Breast cancer Diseases 0.000 description 1
- 208000026310 Breast neoplasm Diseases 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 206010027476 Metastases Diseases 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 208000010191 Osteitis Deformans Diseases 0.000 description 1
- 208000003076 Osteolysis Diseases 0.000 description 1
- 208000001132 Osteoporosis Diseases 0.000 description 1
- 208000027868 Paget disease Diseases 0.000 description 1
- IIDJRNMFWXDHID-UHFFFAOYSA-N Risedronic acid Chemical compound OP(=O)(O)C(P(O)(O)=O)(O)CC1=CC=CN=C1 IIDJRNMFWXDHID-UHFFFAOYSA-N 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229950007593 homonicotinic acid Drugs 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 208000029791 lytic metastatic bone lesion Diseases 0.000 description 1
- 208000027202 mammary Paget disease Diseases 0.000 description 1
- 230000009401 metastasis Effects 0.000 description 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
- C07F9/6503—Five-membered rings
- C07F9/6506—Five-membered rings having the nitrogen atoms in positions 1 and 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/576—Six-membered rings
- C07F9/58—Pyridine rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU1100071A HU230718B1 (hu) | 2011-02-08 | 2011-02-08 | Új eljárás dronsavak gyógyszeripari előállítására |
| PCT/HU2012/000009 WO2012107787A1 (en) | 2011-02-08 | 2012-02-08 | Novel process for the preparation of dronic acids |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EA201300893A1 EA201300893A1 (ru) | 2014-01-30 |
| EA027231B1 true EA027231B1 (ru) | 2017-07-31 |
Family
ID=89990180
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EA201300893A EA027231B1 (ru) | 2011-02-08 | 2012-02-08 | Способ получения бисфосфоновых кислот |
Country Status (7)
| Country | Link |
|---|---|
| EP (1) | EP2673282B1 (lt) |
| EA (1) | EA027231B1 (lt) |
| HU (2) | HU230718B1 (lt) |
| LT (1) | LT2673282T (lt) |
| PL (1) | PL2673282T3 (lt) |
| PT (1) | PT2673282T (lt) |
| WO (1) | WO2012107787A1 (lt) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103030661B (zh) * | 2012-11-16 | 2015-12-02 | 湖南方盛制药股份有限公司 | 伊班膦酸钠的制备方法 |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006134603A1 (en) * | 2005-06-13 | 2006-12-21 | Jubilant Organosys Limited | Process for producing bisphosphonic acids and forms thereof |
| WO2007109542A2 (en) * | 2006-03-21 | 2007-09-27 | Albemarle Corporation | Process for manufacturing bisphosphonic acids |
| WO2008056129A1 (en) * | 2006-11-06 | 2008-05-15 | Hovione Inter Limited | Process for the preparation of biphosphonic acids and salts thereof |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4190615A (en) * | 1978-09-11 | 1980-02-26 | Betz Laboratories, Inc. | Oligomeric ester chain condensates of substituted 1-hydroxy-1,1-diphosphonic acid |
| ES2038692T4 (es) | 1986-11-21 | 2012-02-10 | Novartis Ag | Procedimiento para la obtencion de acidos alcanodifosfonicos substituidos. |
| FR2878248B1 (fr) * | 2004-11-22 | 2007-01-12 | Surfactis Technologies Soc Par | Composes bisphosphoniques pour empecher ou limiter la fixation de macromolecules, de microorganismes et d'un biofilm sur des surfaces solides, notamment metallique ou minerales |
| PL199215B1 (pl) * | 2004-12-28 | 2008-08-29 | Politechnika Gdanska | Sposób wytwarzania kwasu [1-hydroksy-2-(3-pirydylo)etylidenobisfosfonowego] oraz jego soli monosodowej dwu i pół wodnej |
| AR054673A1 (es) | 2005-07-28 | 2007-07-11 | Gador Sa | Una forma cristalina del acido zoledronico, un proceso para su obtencion y la composicion farmaceutica que la comprende |
-
2011
- 2011-02-08 HU HU1100071A patent/HU230718B1/hu not_active IP Right Cessation
-
2012
- 2012-02-08 EA EA201300893A patent/EA027231B1/ru unknown
- 2012-02-08 WO PCT/HU2012/000009 patent/WO2012107787A1/en active Application Filing
- 2012-02-08 HU HUE12716591A patent/HUE031236T2/en unknown
- 2012-02-08 PL PL12716591T patent/PL2673282T3/pl unknown
- 2012-02-08 PT PT127165918T patent/PT2673282T/pt unknown
- 2012-02-08 EP EP12716591.8A patent/EP2673282B1/en not_active Revoked
- 2012-02-08 LT LTEP12716591.8T patent/LT2673282T/lt unknown
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006134603A1 (en) * | 2005-06-13 | 2006-12-21 | Jubilant Organosys Limited | Process for producing bisphosphonic acids and forms thereof |
| WO2007109542A2 (en) * | 2006-03-21 | 2007-09-27 | Albemarle Corporation | Process for manufacturing bisphosphonic acids |
| WO2008056129A1 (en) * | 2006-11-06 | 2008-05-15 | Hovione Inter Limited | Process for the preparation of biphosphonic acids and salts thereof |
Non-Patent Citations (1)
| Title |
|---|
| A. A. PRISHCHENKO ; M. V. LIVANTSOV ; O. P. NOVIKOVA ; L. I. LIVANTSOVA: "Reaction of substituted benzalchlorides with phosphorous acid esters", RUSSIAN JOURNAL OF GENERAL CHEMISTRY, NAUKA/INTERPERIODICA, MO, vol. 76, no. 5, 1 May 2006 (2006-05-01), Mo, pages 835 - 836, XP019407294, ISSN: 1608-3350, DOI: 10.1134/S107036320605029X * |
Also Published As
| Publication number | Publication date |
|---|---|
| HUP1100071A2 (en) | 2012-09-28 |
| EP2673282A1 (en) | 2013-12-18 |
| HU230718B1 (hu) | 2017-11-28 |
| PL2673282T3 (pl) | 2017-05-31 |
| LT2673282T (lt) | 2016-12-12 |
| WO2012107787A1 (en) | 2012-08-16 |
| EP2673282B1 (en) | 2016-11-09 |
| EA201300893A1 (ru) | 2014-01-30 |
| PT2673282T (pt) | 2017-01-06 |
| HUE031236T2 (en) | 2017-09-28 |
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